Bis-(1H-imidazol-2-YL)-methanone → HCID 10784705, compound

HRID 366521Notes

Reaction equation

HRID 366521 reaction equation
[CH2:1]([CH:8]1[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][C:16]#[C:17][C:18]2[CH:19]=[C:20]([NH2:25])[C:21]([NH2:24])=[CH:22][CH:23]=2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:26](C1NC=CN=1)(C1NC=CN=1)=[O:27]>C1COCC1.CCOCC>[CH2:1]([CH:8]1[CH2:9][CH2:10][N:11]([CH2:14][CH2:15][C:16]#[C:17][C:18]2[CH:23]=[CH:22][C:21]3[NH:24][C:26](=[O:27])[NH:25][C:20]=3[CH:19]=2)[CH2:12][CH2:13]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 5250894Bis-(1H-imidazol-2-YL)-methanoneHCID 10830499HCID 10830499, compound

Product 1

HCID 10784705HCID 10784705, compoundYield 64.8%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 4-[4-(4-benzyl-piperidin-1-yl)-but-1-ynyl]-benzene-1,2-diamine (Example 70) (333 mg, 1 mmol) and carbonyl diimidazole (243 mg, 1.5 mmol) in THF (5 mL) is stirred at room temperature for 1 hr. A precipitate forms; the mixture is diluted with ether (10 mL), filtered and the solid washed with ether to give the title compound as a white powder (233 mg): mp 221-223° C.

Workup

  1. filtrationfiltered
  2. washthe solid washed with ether

Sources & evidence

ORD record
ord-cc118e21a5e240f9970429f8cb88c429
Source dataset
uspto-grants-2000_10
Patent number
US06130234

Reaction notes

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